Synthesis of 6-Hydroxysphingosine and 伪-Hydroxy Ceramide Using a Cross-Metathesis Strategy

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• 作者：Patrick Wisse ; Mark A. R. de Geus ; Gen Cross ; Adrianus M. C. H. van den Nieuwendijk ; Eva J. van Rooden ; Richard J. B. H. N. van den Berg ; Johannes M. F. G. Aerts ; Gijsbert A. van der Marel ; Jeroen D. C. Cod茅e ; Herman S. Overkleeft
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：July 17, 2015
• 年：2015
• 卷：80
• 期：14
• 页码：7258-7265
• 全文大小：353K
• ISSN：1520-6904

文摘

In this paper, a new synthetic route toward 6-hydroxysphingosine and 伪-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.